This invention relates to novel diazoles, to herbicidal compositions containing them and to the method of using them for controlling the growth of undesired vegetation.
The control of undesired vegetation is desired in many instances. In the most common situation, it is desired to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
U.S. Pat. No. 4,127,405, issued to Levitt on Nov. 28, 1978, discloses herbicidal sulfonamides of the formula ##STR1## where R.sub.1 is selected from ##STR2## and where W and Q are independently O or S.
U.S. Pat. No. 4,169,719, issued to Levitt on Oct. 2, 1979, discloses pyrimidine compounds corresponding to the triazines disclosed in the '405 patent.
European Patent Application No. 81301874.4, published on Nov. 4, 1981, discloses herbicidal pyrrole sulfonamides of the formulas ##STR3## where R.sub.10 is selected from ##STR4##
European Patent Application No. 80304287.8, published on June 10, 1981, discloses herbicidal compounds of the formulas ##STR5## where W is O or S;
B is ##STR6## R.sub.1 is ##STR7## PA1 Q is ##STR11## R.sub.1 is H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.4 -C.sub.7 cycloalkylalkyl, (R.sub.17 CH).sub.n C(O)R.sub.16, (R.sub.17 CH).sub.n CO.sub.2 R.sub.18, (R.sub.17 CH).sub.n COSR.sub.19, (R.sub.17 CH).sub.n CONR.sub.20 R.sub.21, (R.sub.17 CH).sub.n SO.sub.2 NR.sub.20 R.sub.21, (R.sub.17 CH).sub.n SO.sub.2 R.sub.22, ##STR12## or C.sub.1 -C.sub.6 alkyl substituted either with (a) 1-3 atoms of F, Br or Cl; or PA1 (1) the total number of carbon atoms in R.sub.1 is less than or equal to 8; and PA1 (2) if R.sub.1 is other than C.sub.1 -C.sub.3 alkyl, then R.sub.3 must be H; PA1 R.sub.2, R.sub.3 and R.sub.4 are independently H or CH.sub.3 ; PA1 R.sub.5 is H, C.sub.1 -C.sub.4 alkyl, --OR.sub.6, NO.sub.2, F, Cl, Br, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; PA1 R.sub.6 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.18, SO.sub.2 NR.sub.20 R.sub.21, SO.sub.2 R.sub.22 or C.sub.1 -C.sub.4 alkyl substituted with (a) 1-3 atoms of F, Cl or Br; or (b) OCH.sub.3 ; PA1 (1) when R.sub.5 is other than H, CH.sub.3, OCH.sub.3 or NO.sub.2, then R.sub.6 is H or CH.sub.3 ; and PA1 (2) when R.sub.6 is CO.sub.2 R.sub.18, SO.sub.2 NR.sub.20 R.sub.21 or SO.sub.2 R.sub.22, then R.sub.5 is H, CH.sub.3, OCH.sub.3 or NO.sub.2 ; PA1 R.sub.7 is H or CH.sub.3 ; PA1 R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, --OR.sub.16, NO.sub.2, F, Cl, Br, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; PA1 R.sub.9 is CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.10 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CO.sub.2 R.sub.24, SO.sub.2 NR.sub.20 R.sub.21 or SO.sub.2 R.sub.22 ; PA1 R.sub.11 is H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, --OR.sub.16, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that, when R.sub.10 is other than C.sub.1 -C.sub.3 alkyl, then R.sub.11 is H, Cl, OCH.sub.3, NO.sub.2 or CH.sub.3 ; PA1 R.sub.12 is H or CH.sub.3 ; PA1 R.sub.13 and R.sub.14 are independently H, C.sub.1 -C.sub.3 alkyl --OR.sub.16, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21 ; provided that, when either of R.sub.13 or R.sub.14 is CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21, then the other is H, Cl, CH.sub.3, OCH.sub.3 or NO.sub.2 ; PA1 R.sub.15 is H or CH.sub.3 ; PA1 R.sub.16 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.17 is H or CH.sub.3 ; PA1 R.sub.18 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.19 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.20 and R.sub.21 are independently CH.sub.3 or C.sub.2 H.sub.5 ; PA1 R.sub.22 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 R.sub.23 is H, Cl, Br, CH.sub.3, F, CF.sub.3, OCH.sub.3 or NO.sub.2 ; PA1 R.sub.24 is C.sub.1 -C.sub.3 alkyl or allyl; PA1 R.sub.25 is C.sub.1 -C.sub.3 alkyl; PA1 m is 0, 1 or 2; PA1 n is 0 or 1; PA1 A is ##STR13## X is CH.sub.3, OCH.sub.3, Cl, F, OCF.sub.2 H or SCF.sub.2 H; Y is CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2, OCH.sub.2 CF.sub.3, OCF.sub.3, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or GCF.sub.2 T where G is O or S and T is H, CHClF, CHBrF, CF.sub.2 H or CHFCF.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is H, Cl, CH.sub.3, OCH.sub.3 or OCF.sub.2 H; PA1 X.sub.2 is OCH.sub.3, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.3, SCH.sub.3 or SCH.sub.2 CH.sub.3 ; PA1 Y.sub.2 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA1 X.sub.3 is OCH.sub.3 or CH.sub.3 ; PA1 when X is Cl or F, then Z is CH and Y is OCH.sub.3, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 1a. Compounds of Preferred 1 where A is A-1, and Z is CH. PA1 1b. Compounds of Preferred 1a where X is CH.sub.3, Cl, OCH.sub.3 or OCF.sub.2 H and Y is CH.sub.3, OCH.sub.3 or OCF.sub.2 H. PA1 1c. Compounds of Preferred 1b where R.sub.1 is H or C.sub.1 -C.sub.4 alkyl, and R.sub.3 is H. PA1 2a. Compounds of Preferred 2 where A is A-1, Z is CH and R.sub.4 is H. PA1 2b. Compounds of Preferred 2a where X is CH.sub.3, Cl, OCH.sub.3 or OCF.sub.2 H and Y is CH.sub.3, OCH.sub.3 or OCF.sub.2 H. PA1 2c. Compounds of Preferred 2b where R.sub.5 is H, CH.sub.3, OCH.sub.3, Cl, NO.sub.2, CO.sub.2 R.sub.24 or SO.sub.2 NR.sub.20 R.sub.21 and R.sub.6 is H or C.sub.1 -C.sub.4 alkyl. PA1 3a. Compounds of Preferred 3 where A is A-1, Z is CH and R.sub.7 is H. PA1 3b. Compounds of Preferred 3a where X is CH.sub.3, Cl, OCH.sub.3 or OCF.sub.2 H and Y is CH.sub.3, OCH.sub.3 or OCF.sub.2 H. PA1 3c. Compounds of Preferred 3b where R.sub.8 is Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, Cl, NO.sub.2, CO.sub.2 R.sub.24, S(O).sub.m R.sub.25 or SO.sub.2 NR.sub.20 R.sub.21. PA1 4a. Compounds of Preferred 4 where A is A-1 and Z is CH. PA1 4b. Compounds of Preferred 4a where X is CH.sub.3, Cl, OCH.sub.3 or OCF.sub.2 H and Y is CH.sub.3, OCH.sub.3 or OCF.sub.2 H. PA1 4c. Compounds of Preferred 4b where R.sub.10 is H, C.sub.1 -C.sub.3 alkyl, CO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2 and R.sub.11 is H, CH.sub.3, OCH.sub.3, Cl, Br, NO.sub.2, CO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2. PA1 5a. Compounds of Preferred 5 where A is A-1 and Z is CH. PA1 5b. Compounds of Preferred 5a where X is CH.sub.3, Cl, OCH.sub.3 or OCF.sub.2 H and Y is CH.sub.3, OCH.sub.3 or OCF.sub.2 H. PA1 5c. Compounds of Preferred 5b where R.sub.11 is H, CH.sub.3, OCH.sub.3, Cl, Br, NO.sub.2, CO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2. PA1 6a. Compounds of Preferred 6 where A is A-1 and Z is CH. PA1 6b. Compounds of Preferred 6a where X is CH.sub.3, Cl, OCH.sub.3 or OCF.sub.2 H and Y is CH.sub.3, OCH.sub.3 or OCF.sub.2 H. PA1 6c. Compounds of Preferred 6b where R.sub.13 and R.sub.14 are independently H, CH.sub.3, OCH.sub.3, Cl, Br, NO.sub.2, CO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3 or SO.sub.2 N(CH.sub.3).sub.2.
European Patent Application No. 81302461.9, published on Dec. 9, 1981, discloses herbicidal thiophenesulfonamides of the formula ##STR8## where R.sub.5 is selected from ##STR9##
Nowhere in the art is there any indication that N-[(heterocyclic)aminocarbonyl]diazole sulfonamides could be prepared or that they would possess herbicidal utility.